Leadership

How to Facilitate a Clearing the Air Session for Executive Teams

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The meeting had been running for two hours. The agenda was packed. The slides were polished. And everyone in the room was lying.

Not deliberately. Not maliciously. But when the CEO asked, "Does anyone have concerns about the Q3 direction?" the executive team gave him exactly what he wanted to hear. A few nods. One or two softly worded "we might want to keep an eye on X" comments. Then back to the deck.

I've been in that room more times than I can count. As a facilitator, you learn to read what isn't being said. The slight pause before someone answers. The eye contact that breaks a beat too early. The team member who keeps checking their phone whenever a particular topic comes up. The things that don't get said in executive meetings are often more consequential than the things that do.

That's how teams end up needing a clearing-the-air session in the first place.

Why Executive Teams Let Things Fester

Most leadership team dysfunction doesn't announce itself. It accumulates. A decision made without full buy-in here. A frustration swallowed in a meeting there. A point of view that stops making it into the room because someone learned, at some point, that it wasn't entirely safe to voice it.

By the time a team recognizes it needs to clear the air, they've usually been sitting on these things for months. The dangerous part isn't the conflict itself. It's the polite dishonesty that builds up around it. Teams in this state start to make decisions based on what people are willing to say out loud, rather than what they actually believe. Strategic planning gets filtered. New ideas die before they leave the room. And the executive team, the people most responsible for setting direction, starts operating on a version of reality that's been quietly edited.

Here's the thing: that pattern isn't a character flaw. It's a structural one. Most executive teams were never given the tools for this kind of conversation. They were promoted because they were exceptional individual contributors, or because they scaled revenue, or because they could execute. Not because they were trained in the messy, human work of open dialogue under pressure.

That's exactly what a well-run clearing-the-air session is designed for.

What a Clearing the Air Session Actually Is (and Isn't)

It's not a therapy session. It's not a venting circle. It's not a performance review dressed up as team building.

A clearing-the-air session is a structured conversation designed to bring unspoken tensions, misalignments, and unresolved friction into the open, on the leadership team's terms, in a controlled environment. Done well, it creates the kind of psychological safety that most teams claim to have but rarely do. Research from Amy Edmondson at Harvard has consistently shown that the ability to speak candidly, without fear of repercussion, is one of the strongest predictors of team effectiveness. Google's Project Aristotle confirmed the same thing: it's the foundation.

The goal of a clearing-the-air session isn't to make everyone like each other. The goal is to surface the real issues so the executive team can make better decisions together. Teams that can disagree well, that can hold difficult conversations without it becoming personal, consistently outperform teams that can't.

Read more: High-Performing Teams Need Psychological Safety: Here's How You Can Create It

The Pre-Meeting Work Most Teams Skip

Most clearing-the-air sessions fail before anyone sets foot in the room. Leaders show up without context. Team members haven't had a chance to reflect. The person running it walks in, hoping the conversation will just happen organically.

It won't.

The pre-meeting work is not optional. Before the session, send each member of the leadership team a short set of reflection questions. Keep it simple:

  • What is one thing this team does well that we should protect?
  • What is one pattern you have observed that is getting in the way?
  • What is one thing you have wanted to say in our executive meetings but haven't?

You don't need a formal template. You need honest answers. The point of the pre-work isn't to collect data, it's to prime people for candour. When team members arrive having already named their point of view in writing, the conversation starts at a different depth. You skip the first thirty minutes of throat-clearing that usually happens when people haven't thought it through.

Setting Up the Room

In-person is better for this kind of work. Video calls flatten emotion. They make eye contact harder. They give people too many places to hide.

If you're running this as part of an executive offsite or a broader strategic planning session, even better. A change of environment does something to people that a conference room at the office cannot.

Read more: The Perfect 2-Day Strategy Offsite Agenda for Series B Startups

Before the session opens, establish ground rules explicitly. Not as a formality, but as a genuine contract for the conversation:

What's said here stays here. This is not content for a LinkedIn post or a hallway debrief. It's a safe space for the team to be honest.
Speak from your own experience. "I've noticed..." not "Everyone thinks you..."
No interrupting. A room full of executives is a room full of people used to cutting in. Build a structure where that doesn't happen.
Use a parking lot. If a topic is important but not the right fit for this conversation, it goes in the parking lot. This gives people permission to raise things without derailing the session, and signals that nothing is being dismissed.

These ground rules are the architecture that makes open discussion possible.

Running the Session: A Meeting Agenda That Works

A clearing-the-air session for a leadership team typically runs two to three hours. Any shorter and you won't get past the surface. Any longer and exhaustion starts to look like conflict.

Here's a meeting agenda structure that works:

  1. Opening check-in (15 minutes). Ask each person to share one word or phrase that describes where they are going into this conversation. Not a status update. Not a performance. Just an honest temperature read. It grounds the room.
  2. Appreciations (15 minutes). What is working? What should the team protect? This isn't cheerleading, it's anchoring. Naming what's good before naming what isn't creates a foundation for the harder conversation.
  3. Open discussion (60 to 90 minutes). This is the core of the session. Go around the table and ask each team member to name one pattern they want to put on the table. No debate yet. Just naming. You'll often find that three different people name the same issue using different words. That's where the real work is. The facilitator's role here is to keep the conversation moving, draw out the quieter voices, and prevent anyone from dominating. (Read more: How To Handle Task Conflict and Relationship Conflict as a Manager)
  4. Key takeaways and next steps (30 minutes). What did the team learn? What changes? A conversation without next steps is just a vent session. Before the room closes, the executive team should agree on two or three specific commitments, each with a clear owner. Keep the list short. Follow-through on two things beats grand promises on ten.
  5. Closing check-in (10 minutes). Repeat the opening question. "One word for where you're at now." You will almost always see a visible shift. That shift is the data.

The Follow-Up Is Where It Actually Works or Dies

This is where most clearing-the-air sessions fall apart.

Within 48 hours of the session, someone should send a brief summary of the commitments made. Not a verbatim transcript. Not a slide deck. Just the key takeaways, the decisions, and who owns what. Then build check-ins into the team's operating cadence, not to relitigate what was said, but to make sure the commitments actually land.

The clearing-the-air session is not a one-time fix. It's the beginning of a different way of working together. Teams that do this well treat it as a practice, not a crisis response. They clear the air before things get to the point where clearing it feels urgent.

If the issues were deep enough to require this session, they won't be resolved in an afternoon. The session creates permission for more honest conversation. Your job, as the leader who called the meeting, is to make sure permission doesn't expire the moment people return to their desks.

Read more: The Conflict Resolution Workshop Agenda Your Team Actually Needs

Executive facilitating a clearing the air session with leadership team members across a conference table

The Thing Nobody Tells You About This Work

The hardest part of running a clearing-the-air session isn't managing the conflict. It's managing the silence before it.

Most executive teams don't have these conversations because no one wants to take the initiative. There is a real cost to going first. Someone has to say "we need to talk about the thing we're not talking about," and that's a vulnerable move, even at the top.

But the teams I've seen pull ahead aren't the ones who had perfect communication from the start. They're the ones who were willing to sit in the discomfort, name what wasn't working, and build something better from there.

Read more: The Importance of Building Team Trust

See, effective communication at the executive level isn't about having the right words. It's about creating the conditions where the right words can actually be said. A well-run clearing-the-air session is one of the most direct ways to build that. Not because it's comfortable, but because the alternative, strategic planning and teamwork built on polite dishonesty, catches up with every team eventually.

The question isn't whether your leadership team is carrying unspoken tension into the next quarter. They are. Every team is. The question is whether you're willing to create the space to clear it.

Ready to take that step? If your executive team needs a structured, professionally facilitated conversation, book a Diagnostic Call to talk through what your team needs.

FAQs:

Now that you have mastered how to manage conflict - what is your plan of action for making an impact with your team?

Now that you have mastered how to create an environment of empowerment via the 3-P's - what is your plan of action for making an impact with your team?

Developing Your Communication, Empathy and Emotional Intelligence skills is start. What is your plan of action for implementing your learnings within your your team?

Now that you understand the differences in these titles - what is your plan of action for what you learned?

Assessing your team's behaviors is a start - but do you have a plan of action for the results?

Now that you have mastered the art of decision making - what is your plan of action for making an impact with your team?

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